O-acetylglucal → 4,6-di-O-acetylglucal

Participants

Reaction Steps

Per-O-acetyl glucal (27.5 mmol) was dissolved in phosphorane buffer (80 mL). Amano lipase (4.0 g) was added and the reaction mixture was stirred at room temperature for 24 hr. Brine (200 mL) was added and the obtained mixture was extracted with ethyl acetate (3×150 mL). Combined organic extracts were filtered trough Celite, and dried over anhydrous sodium sulfate. Drying agent and solvent were removed and product was purified by column chromatography (SilicaGel 60) using hexanes:ethyl acetate as eluents. 4,6-Di-O-Acetyl-D-glucal (26 mmol, yield 96%) was obtained.

Provenance & Evidence